Issue contents
Download PDF of article
Download CIF
3D view
Navigation
Highlighting
Dictionary of Crystallography reference
IUPAC Gold Book reference
more ...
Download citation
FormatBIBTeX
EndNote
RefMan
Refer
Medline
CIF
SGML
Plain Text
share
Previous article
Next article
Previous article
Issue contents
Download PDF of article
Download CIF
3D view
Navigation
Highlighting
Dictionary of Crystallography reference
IUPAC Gold Book reference
more ...
Download citation
FormatBIBTeX
EndNote
RefMan
Refer
Medline
CIF
SGML
Plain Text
share
Next article

organic compounds\(\def\hfill{\hskip 5em}\def\hfil{\hskip 3em}\def\eqno#1{\hfil {#1}}\)

Journal logoCRYSTALLOGRAPHIC
COMMUNICATIONS
ISSN: 2056-9890
Volume 68| Part 8| August 2012| Page o2460
https://doi.org/10.1107/S1600536812031625

1-(2,4-Di­fluoro­phen­yl)thio­urea

Hoong-Kun Fun,a*‡ Ching Kheng Quah,a§ Prakash S. Nayak,b B. Narayanab and B. K. Sarojinic

aX-ray Crystallography Unit, School of Physics, Universiti Sains Malaysia, 11800 USM, Penang, Malaysia, bDepartment of Studies in Chemistry, Mangalore University, Mangalagangotri 574 199, India, and cDepartment of Chemistry, P. A. College of Engineering, Nadupadavu, Mangalore 574 153, India
*Correspondence e-mail: hkfun@usm.my

(Received 10 July 2012; accepted 11 July 2012; online 18 July 2012)

The asymmetric unit of the title compound, C7H6F2N2S, consists of two independent mol­ecules, with comparable geometries. In one mol­ecule, the thio­urea moiety is essentially planar (r.m.s. deviation = 0.014 Å) and it forms a dihedral angle of 78.67 (9)° with the benzene ring. The corresponding r.m.s. deviation and dihedral angle for the other mol­ecule are 0.011 Å and 81.71 (8)°, respectively. In both mol­ecules, one of the F atoms is disordered over two positions with refined site occupancies of 0.572 (3):0.428 (3) and 0.909 (2):0.091 (2), respectively. In the crystal, mol­ecules are linked via N—H⋯S and C—H⋯F hydrogen bonds into two-dimensional networks parallel to (010).

Related literature

For general background to and the related structures of the title compound, see: Fun et al. (2012a[Fun, H.-K., Quah, C. K., Nayak, P. S., Narayana, B. & Sarojini, B. K. (2012a). Acta Cryst. E68, o2423.],b[Fun, H.-K., Quah, C. K., Nayak, P. S., Narayana, B. & Sarojini, B. K. (2012b). Acta Cryst. E68, o2462.]); Sarojini et al. (2007[Sarojini, B. K., Narayana, B., Sunil, K., Yathirajan, H. S. & Bolte, M. (2007). Acta Cryst. E63, o3754.]). For standard bond-length data, see: Allen et al. (1987[Allen, F. H., Kennard, O., Watson, D. G., Brammer, L., Orpen, A. G. & Taylor, R. (1987). J. Chem. Soc. Perkin Trans. 2, pp. S1-19.]). For the stability of the temperature controller used for the data collection, see: Cosier & Glazer (1986[Cosier, J. & Glazer, A. M. (1986). J. Appl. Cryst. 19, 105-107.]).

[Scheme 1]

Experimental

Crystal data

  • C7H6F2N2S

  • Mr = 188.20

  • Monoclinic, P 21 /c

  • a = 6.4260 (7) Å

  • b = 36.908 (4) Å

  • c = 6.6821 (7) Å

  • β = 100.464 (2)°

  • V = 1558.4 (3) Å3

  • Z = 8

  • Mo Kα radiation

  • μ = 0.39 mm−1

  • T = 100 K

  • 0.36 × 0.14 × 0.09 mm
Data collection

  • Bruker SMART APEXII DUO CCD area-detector diffractometer

  • Absorption correction: multi-scan (SADABS; Bruker, 2009[Bruker (2009). APEX2, SAINT and SADABS. Bruker AXS Inc., Madison, Wisconsin, USA.]) Tmin = 0.874, Tmax = 0.967

  • 13654 measured reflections

  • 3553 independent reflections

  • 3082 reflections with I > 2σ(I)

  • Rint = 0.031
Refinement

  • R[F2 > 2σ(F2)] = 0.033

  • wR(F2) = 0.077

  • S = 1.06

  • 3553 reflections

  • 255 parameters

  • 4 restraints

  • H atoms treated by a mixture of independent and constrained refinement

  • Δρmax = 0.55 e Å−3

  • Δρmin = −0.36 e Å−3

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A D—H H⋯A D⋯A D—H⋯A
N1A—H1NA⋯S1B 0.794 (19) 2.586 (19) 3.3485 (15) 161.7 (19)
N2A—H2NA⋯S1B 0.81 (2) 2.77 (3) 3.499 (2) 151 (2)
N2A—H3NA⋯S1Bi 0.85 (2) 2.65 (2) 3.504 (2) 175.2 (16)
N1B—H1NB⋯S1Aii 0.88 (2) 2.49 (2) 3.3273 (15) 158.9 (17)
N2B—H2NB⋯S1Aii 0.88 (2) 2.76 (2) 3.5179 (19) 146.4 (18)
N2B—H3NB⋯S1Aiii 0.82 (3) 2.66 (3) 3.4592 (19) 167 (2)
C4B—H4BA⋯F1Bi 0.95 2.50 3.094 (2) 121
C5B—H5BA⋯F1Bi 0.95 2.52 3.111 (2) 121
Symmetry codes: (i) x, y, z+1; (ii) x-1, y, z-1; (iii) x, y, z-1.

Data collection: APEX2 (Bruker, 2009[Bruker (2009). APEX2, SAINT and SADABS. Bruker AXS Inc., Madison, Wisconsin, USA.]); cell refinement: SAINT (Bruker, 2009[Bruker (2009). APEX2, SAINT and SADABS. Bruker AXS Inc., Madison, Wisconsin, USA.]); data reduction: SAINT; program(s) used to solve structure: SHELXTL (Sheldrick, 2008[Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.]); program(s) used to refine structure: SHELXTL; molecular graphics: SHELXTL; software used to prepare material for publication: SHELXTL and PLATON (Spek, 2009[Spek, A. L. (2009). Acta Cryst. D65, 148-155.]).

Supporting information

Crystal structure: contains datablocks global, I. DOI: https://doi.org/10.1107/S1600536812031625/kj2208sup1.cif

Structure factors: contains datablock I. DOI: https://doi.org/10.1107/S1600536812031625/kj2208Isup2.hkl

Supporting information file. DOI: https://doi.org/10.1107/S1600536812031625/kj2208Isup3.cml

checkCIF report


Comment top

In continuation of our work on the synthesis of thiourea derivatives (Fun et al., 2012a, 2012b; Sarojini et al., 2007), the title compound is prepared and its crystal structure is reported here.

The asymmetric unit (Fig. 1) of the title compound consists of two independent molecules (A and B), with comparable geometries. In molecule A, thiourea moiety (S1A/N1A/N2A/C7A) is essentially planar (r.m.s. deviation = 0.014 Å) and it forms a dihedral angle of 78.67 (9)° with the benzene ring (C1A-C6A). The corresponding r.m.s. deviation and dihedral angle for molecule B are 0.011 Å and 81.71 (8)°, respectively. Bond lengths (Allen et al., 1987) and angles are within normal ranges and are comparable to related structures (Fun et al., 2012a, 2012b). The fluorine atoms (F1A/F1B) of both molecules are disordered over two positions with refined site-occupancies of 0.572 (3):0.428 (3) and 0.909 (2): 0.091 (2), respectively.

In the crystal structure, Fig. 2, molecules are linked via intermolecular N—H···S and C—H···F hydrogen bonds (Table 1) into two-dimensional networks parallel to (010).

Related literature top

For general background to and the related structures of the title compound, see: Fun et al. (2012a,b); Sarojini et al. (2007). For standard bond-length data, see: Allen et al. (1987). For the stability of the temperature controller used for the data collection, see: Cosier & Glazer (1986).

Experimental top

2,4-Difluoroaniline (0.84 mL, 0.0081 mol) was refluxed with potassium thiocyanate (1.4 g, 0.0142 mol) in 20 mL of water and 1.6 mL of concentrated HCl for 3 h. The reaction mixture was then cooled to room temperature and stirred overnight. The precipitated product was then filetred, washed with water, dried and recrystallised from acetone and toluene (1:1) mixture by slow evaporation method (m.p. 441-443K).

Refinement top

N-bound hydrogen atoms were located in a difference Fourier map and refined freely with N–H = 0.79 (2)–0.88 (2) Å. The remaining H atoms were positioned geometrically and refined using a riding model with C–H = 0.95 Å and Uiso(H) = 1.2 Ueq(C). The fluorine atoms (F1A/F1B) of both molecules are disordered over two positions with refined site-occupancies of 0.572 (3):0.428 (3) and 0.909 (2): 0.091 (2), respectively. The same Uij parameters were used for atom pair F1B/F1BX.

Structure description top

In continuation of our work on the synthesis of thiourea derivatives (Fun et al., 2012a, 2012b; Sarojini et al., 2007), the title compound is prepared and its crystal structure is reported here.

The asymmetric unit (Fig. 1) of the title compound consists of two independent molecules (A and B), with comparable geometries. In molecule A, thiourea moiety (S1A/N1A/N2A/C7A) is essentially planar (r.m.s. deviation = 0.014 Å) and it forms a dihedral angle of 78.67 (9)° with the benzene ring (C1A-C6A). The corresponding r.m.s. deviation and dihedral angle for molecule B are 0.011 Å and 81.71 (8)°, respectively. Bond lengths (Allen et al., 1987) and angles are within normal ranges and are comparable to related structures (Fun et al., 2012a, 2012b). The fluorine atoms (F1A/F1B) of both molecules are disordered over two positions with refined site-occupancies of 0.572 (3):0.428 (3) and 0.909 (2): 0.091 (2), respectively.

In the crystal structure, Fig. 2, molecules are linked via intermolecular N—H···S and C—H···F hydrogen bonds (Table 1) into two-dimensional networks parallel to (010).

For general background to and the related structures of the title compound, see: Fun et al. (2012a,b); Sarojini et al. (2007). For standard bond-length data, see: Allen et al. (1987). For the stability of the temperature controller used for the data collection, see: Cosier & Glazer (1986).

Computing details top

Data collection: APEX2 (Bruker, 2009); cell refinement: SAINT (Bruker, 2009); data reduction: SAINT (Bruker, 2009); program(s) used to solve structure: SHELXTL (Sheldrick, 2008); program(s) used to refine structure: SHELXTL (Sheldrick, 2008); molecular graphics: SHELXTL (Sheldrick, 2008); software used to prepare material for publication: SHELXTL (Sheldrick, 2008) and PLATON (Spek, 2009).

Figures top
[Figure 1] Fig. 1. The asymmetric unit of the title compound showing 50% probability displacement ellipsoids for non-H atoms. Both major and minor disorder component are shown.
[Figure 2] Fig. 2. The crystal structure of the title compound, viewed along the a axis. H atoms not involved in hydrogen bonds (dashed lines) have been omitted for clarity. Only major component of disorder is shown.
1-(2,4-Difluorophenyl)thiourea top
Crystal data top
C7H6F2N2SF(000) = 768
Mr = 188.20Dx = 1.604 Mg m−3
Monoclinic, P21/cMo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybcCell parameters from 5197 reflections
a = 6.4260 (7) Åθ = 3.2–32.0°
b = 36.908 (4) ŵ = 0.39 mm−1
c = 6.6821 (7) ÅT = 100 K
β = 100.464 (2)°Plate, colourless
V = 1558.4 (3) Å30.36 × 0.14 × 0.09 mm
Z = 8
Data collection top
Bruker SMART APEXII DUO CCD area-detector
diffractometer		3553 independent reflections
Radiation source: fine-focus sealed tube3082 reflections with I > 2σ(I)
Graphite monochromatorRint = 0.031
φ and ω scansθmax = 27.5°, θmin = 1.1°
Absorption correction: multi-scan
(SADABS; Bruker, 2009)		h = −8→8
Tmin = 0.874, Tmax = 0.967k = −47→47
13654 measured reflectionsl = −8→8
Refinement top
Refinement on F2Primary atom site location: structure-invariant direct methods
Least-squares matrix: fullSecondary atom site location: difference Fourier map
R[F2 > 2σ(F2)] = 0.033Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.077H atoms treated by a mixture of independent and constrained refinement
S = 1.06 w = 1/[σ2(Fo2) + (0.0271P)2 + 1.0603P]
where P = (Fo2 + 2Fc2)/3
3553 reflections(Δ/σ)max = 0.001
255 parametersΔρmax = 0.55 e Å−3
4 restraintsΔρmin = −0.36 e Å−3
Crystal data top
C7H6F2N2SV = 1558.4 (3) Å3
Mr = 188.20Z = 8
Monoclinic, P21/cMo Kα radiation
a = 6.4260 (7) ŵ = 0.39 mm−1
b = 36.908 (4) ÅT = 100 K
c = 6.6821 (7) Å0.36 × 0.14 × 0.09 mm
β = 100.464 (2)°
Data collection top
Bruker SMART APEXII DUO CCD area-detector
diffractometer		3553 independent reflections
Absorption correction: multi-scan
(SADABS; Bruker, 2009)		3082 reflections with I > 2σ(I)
Tmin = 0.874, Tmax = 0.967Rint = 0.031
13654 measured reflections
Refinement top
R[F2 > 2σ(F2)] = 0.0334 restraints
wR(F2) = 0.077H atoms treated by a mixture of independent and constrained refinement
S = 1.06Δρmax = 0.55 e Å−3
3553 reflectionsΔρmin = −0.36 e Å−3
255 parameters
Special details top

Experimental. The crystal was placed in the cold stream of an Oxford Cryosystems Cobra open-flow nitrogen cryostat (Cosier & Glazer, 1986) operating at 100.0 (1) K.

Geometry. All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes.

Refinement. Refinement of F2 against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F2, conventional R-factors R are based on F, with F set to zero for negative F2. The threshold expression of F2 > 2sigma(F2) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F2 are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top
xyzUiso*/UeqOcc. (<1)
F1A0.9955 (3)0.14057 (5)0.6462 (3)0.0235 (5)0.572 (3)
F1AX0.4561 (4)0.21131 (7)0.3297 (4)0.0259 (7)0.428 (3)
F2A1.13116 (19)0.26104 (3)0.46796 (18)0.0356 (3)
S1A0.59786 (6)0.167502 (10)0.91274 (6)0.01619 (10)
N1A0.5812 (2)0.14793 (4)0.5240 (2)0.0209 (3)
N2A0.4287 (3)0.10890 (4)0.7173 (3)0.0227 (3)
C1A0.9376 (3)0.17296 (5)0.5676 (3)0.0223 (4)
H1AA0.98990.15050.62510.027*0.428 (3)
C2A1.0788 (3)0.20077 (5)0.5578 (3)0.0240 (4)
H2AA1.22580.19800.60900.029*
C3A0.9968 (3)0.23273 (5)0.4704 (3)0.0227 (4)
C4A0.7859 (3)0.23758 (5)0.3885 (3)0.0221 (4)
H4AA0.73570.25970.32460.027*
C5A0.6497 (3)0.20898 (5)0.4030 (3)0.0207 (4)
H5AA0.50350.21160.34750.025*0.572 (3)
C6A0.7219 (3)0.17666 (4)0.4967 (3)0.0193 (3)
C7A0.5343 (2)0.13960 (4)0.7068 (3)0.0167 (3)
F1B−0.1368 (2)0.05450 (3)−0.13223 (17)0.0289 (3)0.909 (2)
F1BX−0.1259 (12)0.0838 (3)0.5203 (17)0.0289 (3)0.091 (2)
F2B−0.33235 (18)−0.03440 (3)0.29943 (18)0.0313 (3)
S1B0.32399 (6)0.086866 (11)0.19944 (6)0.01690 (10)
N1B−0.0833 (2)0.10552 (4)0.1680 (2)0.0178 (3)
N2B0.1372 (3)0.15004 (4)0.0948 (2)0.0204 (3)
C1B−0.1715 (2)0.04402 (5)0.0510 (3)0.0195 (3)
H1BA−0.14840.0513−0.07960.023*0.091 (2)
C2B−0.2367 (2)0.00890 (5)0.0765 (3)0.0207 (3)
H2BA−0.2598−0.0080−0.03270.025*
C3B−0.2663 (2)−0.00024 (4)0.2694 (3)0.0201 (3)
C4B−0.2367 (3)0.02342 (5)0.4308 (3)0.0226 (4)
H4BA−0.26060.01610.56100.027*
C5B−0.1706 (3)0.05838 (5)0.3979 (3)0.0205 (3)
H5BA−0.14740.07520.50740.025*0.909 (2)
C6B−0.1382 (2)0.06909 (4)0.2074 (3)0.0163 (3)
C7B0.1138 (3)0.11572 (4)0.1495 (2)0.0157 (3)
H1NA0.538 (3)0.1354 (5)0.429 (3)0.018 (5)*
H2NA0.390 (3)0.0967 (6)0.617 (4)0.026 (6)*
H3NA0.396 (3)0.1029 (5)0.831 (3)0.020 (5)*
H1NB−0.190 (3)0.1202 (6)0.124 (3)0.024 (5)*
H2NB0.028 (3)0.1640 (6)0.052 (3)0.026 (5)*
H3NB0.249 (4)0.1570 (6)0.067 (3)0.025 (6)*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
F1A0.0242 (9)0.0180 (9)0.0258 (10)0.0068 (7)−0.0019 (7)0.0057 (7)
F1AX0.0195 (12)0.0277 (14)0.0287 (14)0.0035 (9)0.0000 (10)0.0036 (11)
F2A0.0395 (6)0.0311 (6)0.0365 (7)−0.0152 (5)0.0080 (5)0.0054 (5)
S1A0.01840 (19)0.01375 (19)0.0162 (2)−0.00093 (14)0.00254 (15)−0.00129 (15)
N1A0.0306 (8)0.0157 (7)0.0157 (7)−0.0058 (6)0.0022 (6)−0.0030 (6)
N2A0.0322 (8)0.0169 (7)0.0195 (8)−0.0079 (6)0.0057 (7)−0.0034 (6)
C1A0.0331 (9)0.0172 (8)0.0179 (8)0.0043 (7)0.0081 (7)0.0019 (7)
C2A0.0246 (9)0.0289 (9)0.0195 (9)0.0003 (7)0.0072 (7)0.0013 (7)
C3A0.0323 (9)0.0200 (8)0.0180 (8)−0.0069 (7)0.0101 (7)−0.0009 (7)
C4A0.0350 (9)0.0161 (8)0.0162 (8)0.0014 (7)0.0070 (7)0.0025 (7)
C5A0.0277 (9)0.0205 (8)0.0136 (8)0.0010 (7)0.0025 (7)−0.0015 (7)
C6A0.0297 (9)0.0151 (8)0.0137 (8)−0.0027 (6)0.0060 (7)−0.0024 (6)
C7A0.0167 (7)0.0144 (7)0.0180 (8)0.0028 (6)0.0006 (6)−0.0005 (6)
F1B0.0454 (7)0.0278 (6)0.0145 (6)−0.0080 (5)0.0084 (5)−0.0017 (5)
F1BX0.0454 (7)0.0278 (6)0.0145 (6)−0.0080 (5)0.0084 (5)−0.0017 (5)
F2B0.0443 (7)0.0172 (5)0.0334 (6)−0.0111 (5)0.0098 (5)0.0002 (5)
S1B0.01641 (18)0.01577 (19)0.0178 (2)0.00075 (14)0.00125 (15)−0.00053 (16)
N1B0.0161 (7)0.0138 (7)0.0231 (7)0.0012 (5)0.0029 (6)0.0021 (6)
N2B0.0190 (7)0.0161 (7)0.0265 (8)0.0003 (6)0.0053 (6)0.0039 (6)
C1B0.0200 (8)0.0221 (8)0.0171 (8)−0.0005 (6)0.0050 (6)0.0015 (7)
C2B0.0230 (8)0.0189 (8)0.0205 (8)−0.0031 (6)0.0044 (7)−0.0052 (7)
C3B0.0203 (8)0.0143 (8)0.0255 (9)−0.0026 (6)0.0034 (7)0.0014 (7)
C4B0.0285 (9)0.0215 (9)0.0176 (8)−0.0020 (7)0.0034 (7)0.0022 (7)
C5B0.0236 (8)0.0185 (8)0.0181 (8)0.0002 (6)0.0003 (7)−0.0028 (7)
C6B0.0125 (7)0.0137 (7)0.0224 (9)0.0004 (6)0.0020 (6)0.0002 (6)
C7B0.0197 (8)0.0166 (8)0.0104 (7)−0.0011 (6)0.0020 (6)−0.0022 (6)
Geometric parameters (Å, º) top
F1A—C1A1.331 (2)F1B—C1B1.341 (2)
F1AX—C5A1.254 (3)F1BX—C5B1.242 (12)
F2A—C3A1.3572 (19)F2B—C3B1.3567 (19)
S1A—C7A1.7079 (17)S1B—C7B1.7049 (16)
N1A—C7A1.346 (2)N1B—C7B1.348 (2)
N1A—C6A1.427 (2)N1B—C6B1.427 (2)
N1A—H1NA0.79 (2)N1B—H1NB0.88 (2)
N2A—C7A1.329 (2)N2B—C7B1.334 (2)
N2A—H2NA0.81 (2)N2B—H2NB0.88 (2)
N2A—H3NA0.85 (2)N2B—H3NB0.82 (2)
C1A—C2A1.379 (3)C1B—C2B1.382 (2)
C1A—C6A1.387 (3)C1B—C6B1.383 (2)
C1A—H1AA0.9500C1B—H1BA0.9500
C2A—C3A1.377 (3)C2B—C3B1.378 (3)
C2A—H2AA0.9500C2B—H2BA0.9500
C3A—C4A1.379 (3)C3B—C4B1.374 (2)
C4A—C5A1.386 (2)C4B—C5B1.389 (2)
C4A—H4AA0.9500C4B—H4BA0.9500
C5A—C6A1.387 (2)C5B—C6B1.384 (2)
C5A—H5AA0.9500C5B—H5BA0.9500
C7A—N1A—C6A122.52 (15)C7B—N1B—C6B123.25 (14)
C7A—N1A—H1NA119.4 (15)C7B—N1B—H1NB118.8 (14)
C6A—N1A—H1NA117.9 (15)C6B—N1B—H1NB116.1 (13)
C7A—N2A—H2NA121.1 (16)C7B—N2B—H2NB121.6 (14)
C7A—N2A—H3NA118.6 (14)C7B—N2B—H3NB120.5 (15)
H2NA—N2A—H3NA120 (2)H2NB—N2B—H3NB115 (2)
F1A—C1A—C2A123.22 (18)F1B—C1B—C2B119.17 (15)
F1A—C1A—C6A114.43 (17)F1B—C1B—C6B117.95 (15)
C2A—C1A—C6A122.35 (16)C2B—C1B—C6B122.88 (16)
C2A—C1A—H1AA118.8C2B—C1B—H1BA118.6
C6A—C1A—H1AA118.8C6B—C1B—H1BA118.6
C3A—C2A—C1A116.96 (17)C3B—C2B—C1B116.17 (16)
C3A—C2A—H2AA121.5C3B—C2B—H2BA121.9
C1A—C2A—H2AA121.5C1B—C2B—H2BA121.9
F2A—C3A—C2A117.99 (16)F2B—C3B—C4B118.46 (16)
F2A—C3A—C4A118.49 (16)F2B—C3B—C2B117.77 (15)
C2A—C3A—C4A123.51 (17)C4B—C3B—C2B123.76 (16)
C3A—C4A—C5A117.47 (16)C3B—C4B—C5B117.95 (16)
C3A—C4A—H4AA121.3C3B—C4B—H4BA121.0
C5A—C4A—H4AA121.3C5B—C4B—H4BA121.0
F1AX—C5A—C4A120.96 (19)F1BX—C5B—C6B109.6 (6)
F1AX—C5A—C6A117.52 (19)F1BX—C5B—C4B129.6 (6)
C4A—C5A—C6A121.52 (17)C6B—C5B—C4B120.84 (16)
C4A—C5A—H5AA119.2C6B—C5B—H5BA119.6
C6A—C5A—H5AA119.2C4B—C5B—H5BA119.6
C5A—C6A—C1A118.07 (16)C1B—C6B—C5B118.40 (15)
C5A—C6A—N1A121.93 (16)C1B—C6B—N1B120.01 (15)
C1A—C6A—N1A120.00 (15)C5B—C6B—N1B121.51 (15)
N2A—C7A—N1A116.32 (16)N2B—C7B—N1B116.42 (15)
N2A—C7A—S1A121.39 (14)N2B—C7B—S1B121.45 (13)
N1A—C7A—S1A122.25 (13)N1B—C7B—S1B122.11 (12)
F1A—C1A—C2A—C3A179.30 (18)F1B—C1B—C2B—C3B179.05 (14)
C6A—C1A—C2A—C3A−1.0 (3)C6B—C1B—C2B—C3B−0.44 (14)
C1A—C2A—C3A—F2A176.87 (16)C1B—C2B—C3B—F2B179.36 (14)
C1A—C2A—C3A—C4A−2.1 (3)C1B—C2B—C3B—C4B0.66 (15)
F2A—C3A—C4A—C5A−176.43 (15)F2B—C3B—C4B—C5B−179.51 (14)
C2A—C3A—C4A—C5A2.5 (3)C2B—C3B—C4B—C5B−0.8 (2)
C3A—C4A—C5A—F1AX−179.1 (2)C3B—C4B—C5B—F1BX−176.9 (4)
C3A—C4A—C5A—C6A0.2 (3)C3B—C4B—C5B—C6B0.7 (2)
F1AX—C5A—C6A—C1A176.2 (2)F1B—C1B—C6B—C5B−179.09 (14)
C4A—C5A—C6A—C1A−3.1 (3)C2B—C1B—C6B—C5B0.4 (2)
F1AX—C5A—C6A—N1A−4.8 (3)F1B—C1B—C6B—N1B4.3 (2)
C4A—C5A—C6A—N1A175.88 (16)C2B—C1B—C6B—N1B−176.21 (13)
F1A—C1A—C6A—C5A−176.79 (16)F1BX—C5B—C6B—C1B177.5 (4)
C2A—C1A—C6A—C5A3.5 (3)C4B—C5B—C6B—C1B−0.6 (2)
F1A—C1A—C6A—N1A4.3 (2)F1BX—C5B—C6B—N1B−5.9 (4)
C2A—C1A—C6A—N1A−175.43 (16)C4B—C5B—C6B—N1B176.01 (15)
C7A—N1A—C6A—C5A−107.0 (2)C7B—N1B—C6B—C1B−79.0 (2)
C7A—N1A—C6A—C1A71.9 (2)C7B—N1B—C6B—C5B104.47 (19)
C6A—N1A—C7A—N2A−169.70 (16)C6B—N1B—C7B—N2B174.25 (15)
C6A—N1A—C7A—S1A12.6 (2)C6B—N1B—C7B—S1B−7.4 (2)
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
N1A—H1NA···S1B0.794 (19)2.586 (19)3.3485 (15)161.7 (19)
N2A—H2NA···S1B0.81 (2)2.77 (3)3.499 (2)151 (2)
N2A—H3NA···S1Bi0.85 (2)2.65 (2)3.504 (2)175.2 (16)
N1B—H1NB···S1Aii0.88 (2)2.49 (2)3.3273 (15)158.9 (17)
N2B—H2NB···S1Aii0.88 (2)2.76 (2)3.5179 (19)146.4 (18)
N2B—H3NB···S1Aiii0.82 (3)2.66 (3)3.4592 (19)167 (2)
C4B—H4BA···F1Bi0.952.503.094 (2)121
C5B—H5BA···F1Bi0.952.523.111 (2)121
Symmetry codes: (i) x, y, z+1; (ii) x−1, y, z−1; (iii) x, y, z−1.

Experimental details

Crystal data
Chemical formulaC7H6F2N2S
Mr188.20
Crystal system, space groupMonoclinic, P21/c
Temperature (K)100
a, b, c (Å)6.4260 (7), 36.908 (4), 6.6821 (7)
β (°) 100.464 (2)
V (Å3)1558.4 (3)
Z8
Radiation typeMo Kα
µ (mm−1)0.39
Crystal size (mm)0.36 × 0.14 × 0.09
Data collection
DiffractometerBruker SMART APEXII DUO CCD area-detector
Absorption correctionMulti-scan
(SADABS; Bruker, 2009)
Tmin, Tmax0.874, 0.967
No. of measured, independent and
observed [I > 2σ(I)] reflections		13654, 3553, 3082
Rint0.031
(sin θ/λ)max (Å−1)0.650
Refinement
R[F2 > 2σ(F2)], wR(F2), S 0.033, 0.077, 1.06
No. of reflections3553
No. of parameters255
No. of restraints4
H-atom treatmentH atoms treated by a mixture of independent and constrained refinement
Δρmax, Δρmin (e Å−3)0.55, −0.36

Computer programs: APEX2 (Bruker, 2009), SAINT (Bruker, 2009), SHELXTL (Sheldrick, 2008) and PLATON (Spek, 2009).

Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
N1A—H1NA···S1B0.794 (19)2.586 (19)3.3485 (15)161.7 (19)
N2A—H2NA···S1B0.81 (2)2.77 (3)3.499 (2)151 (2)
N2A—H3NA···S1Bi0.85 (2)2.65 (2)3.504 (2)175.2 (16)
N1B—H1NB···S1Aii0.88 (2)2.49 (2)3.3273 (15)158.9 (17)
N2B—H2NB···S1Aii0.88 (2)2.76 (2)3.5179 (19)146.4 (18)
N2B—H3NB···S1Aiii0.82 (3)2.66 (3)3.4592 (19)167 (2)
C4B—H4BA···F1Bi0.95002.50003.094 (2)121.00
C5B—H5BA···F1Bi0.95002.52003.111 (2)121.00
Symmetry codes: (i) x, y, z+1; (ii) x−1, y, z−1; (iii) x, y, z−1.
 

Footnotes

‡Thomson Reuters ResearcherID: A-3561-2009.

§Thomson Reuters ResearcherID: A-5525-2009

Acknowledgements

The authors would like to thank Universiti Sains Malaysia for a Research University Grant (No. 1001/PFIZIK/811160). BN thanks the UGC for financial assistance through SAP and a BSR one-time grant for the purchase of chemicals.

References

First citationAllen, F. H., Kennard, O., Watson, D. G., Brammer, L., Orpen, A. G. & Taylor, R. (1987). J. Chem. Soc. Perkin Trans. 2, pp. S1–19.  CSD CrossRef Web of Science Google Scholar
 First citationBruker (2009). APEX2, SAINT and SADABS. Bruker AXS Inc., Madison, Wisconsin, USA.  Google Scholar
 First citationCosier, J. & Glazer, A. M. (1986). J. Appl. Cryst. 19, 105–107.  CrossRef CAS Web of Science IUCr Journals Google Scholar
 First citationFun, H.-K., Quah, C. K., Nayak, P. S., Narayana, B. & Sarojini, B. K. (2012a). Acta Cryst. E68, o2423.  CSD CrossRef IUCr Journals Google Scholar
 First citationFun, H.-K., Quah, C. K., Nayak, P. S., Narayana, B. & Sarojini, B. K. (2012b). Acta Cryst. E68, o2462.  CSD CrossRef IUCr Journals Google Scholar
 First citationSarojini, B. K., Narayana, B., Sunil, K., Yathirajan, H. S. & Bolte, M. (2007). Acta Cryst. E63, o3754.  Web of Science CSD CrossRef IUCr Journals Google Scholar
 First citationSheldrick, G. M. (2008). Acta Cryst. A64, 112–122.  Web of Science CrossRef CAS IUCr Journals Google Scholar
 First citationSpek, A. L. (2009). Acta Cryst. D65, 148–155.  Web of Science CrossRef CAS IUCr Journals Google Scholar

This is an open-access article distributed under the terms of the Creative Commons Attribution (CC-BY) Licence, which permits unrestricted use, distribution, and reproduction in any medium, provided the original authors and source are cited.

Journal logoCRYSTALLOGRAPHIC
COMMUNICATIONS
ISSN: 2056-9890
Volume 68| Part 8| August 2012| Page o2460
https://doi.org/10.1107/S1600536812031625
Follow Acta Cryst. E
Sign up for e-alerts
E-alerts
Follow Acta Cryst. on Twitter
Twitter
Follow us on facebook
Facebook
Sign up for RSS feeds
RSS